When he was still a manager Kevin Keegan was not always the paranoid, haunted soul of popular memory. He was the sort of manager who would say hello to the kid on work experience and make self-deprecating jokes after games that he might lose his job.

It was a personal view that he was a decent man. Like just about every Newcastle fan, I would like to see him take Mike Ashley to the cleaners this week in his compensation claim for constructive dismissal. For some people Keegan's lawsuit is a straight choice between a good football man who loved Newcastle and an owner who put player transfers in the hands of Dennis Wise and his cronies.

It sounds like an open-and-shut case. The two signings that Keegan is understood to have based his claim upon are Xisco – £5.7m from Deportivo La Coruña on the last day of the transfer window in September 2008 – and Jonas Gutierrez from Real Mallorca for a fee that climbed eventually to £5.2m.

Those two, Keegan will contest, were bought behind his back. What is more, they were disastrous. Xisco made three league starts; Gutierrez did not score his first goal until a pre-season friendly against Darlington this summer, which was way too late to save Newcastle from relegation. Throw in the loan signing of the equally hapless Nacho Gonzalez from Valencia that was allegedly unsanctioned by Keegan and you have what seems like a compelling case.

Told from this point of view, it reads as the story of a regime not simply acquiring players without their manager's approval, but one that acquired players so inadequate they could only contribute to the manager's failure. But there is one question that nags away. It goes to the heart of Keegan's more recent record as a manager. And that question is: could he have done any better himself? Some people remember Keegan as a brilliant intuitive forward at Liverpool and then twice European Footballer of the Year at Hamburg. My generation remember him more for when he was Newcastle manager in the 1990s and built a stupendously attacking team. Others will remember his promotion with Fulham. Many will remember him as the England manager who resigned in the Wembley toilets.

Not many recall his time at Manchester City where he was manager for four years. It was his last job before he disappeared from football in March 2005 for almost three years until he was dramatically recalled by Newcastle. At City he won promotion to the Premier League in 2002 and then just drifted along with limited success until he left suddenly in March 2005.

Keegan's record of signings at City suggested a manager whose once-sure touch in the transfer market had deserted him. Whether it was worse than Newcastle's record of allegedly buying players without his assent is debatable. What was not in doubt was that the players Keegan brought to City were his downfall.

Matias Vuoso for £3.5m from Independiente was the worst of the lot. He never played a single game. But there were others. Lucien Mettomo and Christian Negouai cost a total of £3m; Jon Macken was dramatically overpriced at £5.5m from Preston and there was £3.5m for the accident-prone David Sommeil.

Robbie Fowler came for £6m in a row that caused the chairman David Bernstein to quit. He was not an unqualified failure but he was well past his best and became an embarrassment for Keegan when he was pictured smoking and drinking in a nightclub on an away trip. Steve McManaman was a free transfer but on big wages. He never scored a single goal for City.

There were others too. Players like Mikkel Bischoff and Kevin Ellegaard, signed for £750,000 each who barely made an impression. Keegan was unlucky with the injuries that Claudio Reyna and Trevor Sinclair suffered but really the rest of the misfortune was of his own making. The then-chairman John Wardle found £13m for him to sign Nicolas Anelka from Paris St-Germain but he was hardly an undiscovered talent – or a bargain.

The misjudgement that Newcastle fans made when Keegan returned to their club was to remember the great days of the 1995-96 season and conveniently forget everything that happened in between. Yes, this was the man who signed John Beresford, Scott Sellars, Rob Lee, Andy Cole, Philippe Albert, Peter Beardsley, David Ginola, Les Ferdinand and Alan Shearer. But this was also the man who later signed Vuoso, Bischoff, Mettomo and McManaman.

That was the flaw at the heart of Keegan's return. It is wonderful to have empathy with the supporters of the club you manage. When Keegan talked about the West Stanley pit disaster in 1909 – at which his grandfather Frank was a rescuer – you sensed a connection with place and history that was rare in modern English football between manager and supporters.

The problem for Keegan was that there is so much more to it than that. At City he was already showing signs that, if he was not out of love with football then he was out of love with football management.

He should never have come back. Something tells me that if he is successful and takes £9m from Ashley this week, it may soften the blow.

In the transfer jungle Leeds bite the hand that fed

The Leeds United chief executive, Shaun Harvey, got very self-righteous when he described Everton as a "predator club" for signing Luke Garbutt, 16, from their academy. "Perhaps now is the time to start considering points deductions," Harvey said.

Funny that, because I don't remember Leeds complaining too much when they offloaded another teenager, Aaron Lennon, then 18, to Tottenham in June 2005. In fact, they were desperate for the £1m they got for him to keep the club afloat amid financial difficulties all of their own making. One club's predator is another's lifesaver. Or in Leeds' world, maybe they are one and the same thing.

World Cup will always be bigger than the sum of missing parts

Please, no tears for Cristiano Ronaldo, Lionel Messi or Thierry Henry if their respective nations do not make it to the World Cup finals next summer. It will be no less of an occasion without them, just different. No one bar the host country has the right to be there, you have to earn it in qualification.

It will not cheapen the tournament if Portugal, Argentina or France are not in it; no more than Spain believe that their Euro 2008 title is worth any less because England were not at the tournament. That's the beauty of international football. You can sign for any club team in the world, but you are stuck with your country.

Adebayor's fleet feat

The most extraordinary aspect of Emmanuel Adebayor's 90-yard sprint to goad the Arsenal fans on Saturday? There were times when, at his most disillusioned last season, the striker did not run that far in a whole game.